Color-photographic recording material

Abstract

Compounds which contain in their molecule both a hydroquinone monoether or resorcinol monoether radical and a polyalkylpiperidine radical are effective stabilizers for photographic dyes and their intermediates. In particular, they act as stabilizers against damage by light.

What is claimed is: 
     
       1. A compound of the formula   [A].sub.a Z--B].sub.b                                      (I)     in which a and b independently of one another are integers from 1 to 5 and (a+b) is a number from 2 to 6, A is a monovalent hydroquinone monoether or resorcinol monoether radical, the free OH group of which is sterically hindered, Z is an (a+b)-valent organic radical linking groups A and B and B is a monovalent polyalkylpiperidine radical of the formula II or III ##STR34## in which R is hydrogen or methyl, X is a group ##STR35## or a 5-membered or 6-membered heterocyclic spiro ring with two O or N atoms, Y is a group --CH 2  -- or --CH(R 2 )-- or a 5-membered or 6-membered heterocyclic spiro ring with two O or N atoms, R 1  is hydroxyl, C 1  -C 12  -alkyl, C 3  -C 6  -alkenyl, C 3  -C 4  -alkynyl, C 7  -C 12  -phenylalkyl, glycidyl, C 1  -C 4  -alkyl which is substituted by halogen, --CN, --COOR 3  or --CON(R 4 )(R 5 ), a group --CO--R 6 , --CO--OR 3 , --CO--N(R 4 )(R 5 ), --CH 2  --CH(R 7 )--OR 8 , --SO--R 9 , --SO 2  --R 9 , --OR 3  or --OOC--R 6 , or a group --Z o  --A, in which Z o  is a divalent organic radical, and, if b is 1, R 1  can also be a group of the formula ##STR36## in which p is 1, 2 or 3 and, if p is 1, M is a divalent group and is C 2  -C 12  -alkylene, C 4  -C 8  -alkenylene, xylylene or a radical of the formula --CH 2  C.tbd.C--CH 2  --) ##STR37## --CH 2  --COO--R 10  --OOC--CH 2  --, --CH 2  --CH(OH)--CH 2  --, --CH 2  CH(OH)CH 2  --D--CH 2  CH(OH)CH 2  --, --CH 2  --CH(R 7 )--OOC--R 11  --COO--CH(R 7 )--CH 2  -- or --CO--NH--G--NH--CO--, in which D is a divalent radical of the formula --O--R 12  --O-- or --OOC--R 11  --COO-- and G is a divalent aliphatic, cycloaliphatic, aromatic or aromatic-aliphatic radical having 6-15 C atoms, or, if p is 2, M is a trivalent radical of the formula     T--CH.sub.2 CH(OH)CH.sub.2 ].sub.3 or R.sup.13 --COO--CH(R.sup.7)--CH.sub.2 ].sub.3     in which T is a trivalent radical of the formula ##STR38## or, if p is 3, M is a quadrivalent radical of the formula     Q--CH.sub.2 CH(OH)CH.sub.2 ].sub.4 or R.sup.14 --COO--CH(R.sup.7)--CH.sub.2 ].sub.4     in which Q is a group of the formula ##STR39## R 2  is hydroxyl, --OR 15 , --OOC--R 6 , --OOC--N(R 4 )(R 5 ), --N(R 16 )--CO--R 6  or --N(R 16 )--CO--N(R 4 )(R 5 ), or is a group --Z o  --A, and, if b is 1, R 2  can also be a group of the formula ##STR40## in which r is 1, 2 or 3 and, if r is 1, M' is a divalent group of the formula --OOC--R 11  --COO--, --OOC--NH--G--NH--COO--, --N(R 16 )--CO--R 11  --CO--N--(R 16 )-- or --N(R 17 )--R 18  --N(R 17 )--, or, if r is 2, M' is a trivalent group of the formula     R.sup.19 [COO].sub.3 or R.sup.19 [CON(R.sup.16)].sub.3     or, if r is 3, M' is a quadrivalent group of the formula     R.sup.20 [COO].sub.4 or R.sup.20 [CON(R.sup.16)].sub.3     R 3  is C 1  -C 12  -alkyl, benzyl or cyclohexyl, R 4  is C 1  -C 12  -alkyl, allyl, cyclohexyl, benzyl or phenyl and R 5  is hydrogen, C 1  -C 8  -alkyl or allyl, or R 4  and R 5 , together with the N atom, are a 5-membered or 6-membered heterocyclic ring, R 6  is hydrogen, C 1  -C 12  -alkyl, C 2  -C 6  -alkenyl, chloromethyl, C 5  -C 12  -cycloalkyl, C 7  -C 12  -phenylalkyl, phenyl, C 7  -C 10  -alkylphenyl, or phenyl, phenylmethyl or phenethyl which is substituted by 1 or 2 C 1  -C 4  -alkyl groups and a hydroxyl group, R 7  is hydrogen, C 1  -C 4  -alkyl, C 2  -C 13  -alkoxymethyl, phenyl or phenoxymethyl, R 8  is hydrogen, C 1  -C 12  -alkyl, --CO--R 6  or --CO--N(R 4 )(R 5 ), R 9  is C 1  -C 12  -alkyl, phenyl or C 7  -C 22  -alkylaryl, R 10  is C 2  -C 12  -alkylene, C 4  -C 8  -oxaalkylene or cyclohexylene, R 11  is a direct bond, C 1  -C 12  -alkylene, C 2  -C 6  -alkenylene, C 6  -C 12  -cycloalkylene or -cycloalkenylene or C 6  -C 12  -arylene, R 12  is C 2  -C 12  -alkylene, C 6  -C 12  -cycloalkylene, C 6  -C 12  -arylene or -phenylene-W-phenylene- and W is --O--, --CH 2  --, >C(CH 3 ) 2  or --SO 2  --, R 13  is a trivalent aliphatic hydrocarbon radical having 3-10 carbon atoms or a trivalent aromatic hydrocarbon radical having 6-10 C atoms, R 14  is a quadrivalent aliphatic hydrocarbon radical having 4-10 C atoms or a quadrivalent aromatic hydrocarbon radical having 6-12 C atoms, R 15  is hydrogen, C 1  -C 12  -alkyl, allyl or benzyl, R 16  is hydrogen, C 1  -C 12  -alkyl, C 5  -C 12  -cycloalkyl or benzyl, R 17  is hydrogen, C 1  -C 12  -alkyl, allyl, benzyl, C 2  - C 12  -alkanoyl or benzoyl, R 18  is C 2  -C 12  -alkylene, C 4  -C 16  -alkylene which is interrupted by one or more --O-- or --N(R 16 )--, or C 6  -C 12  -cycloalkylene, R 19  is a trivalent aliphatic radical having 3-10 C atoms, a trivalent aromatic radical having 6-10 C atoms or the group N(CH 2 ) 3  and R 20  is a quadrivalent aliphatic radical having 4-10 C atoms or a quadrivalent aromatic radical having 6-12 C atoms.   
     
     
       2. A compound according to claim 1 of the formula ##STR41## in which a and b independently of one another are numbers from 1 to 3 and (a+b) is a number from 2 to 4, R a  is a monovalent hydrocarbon radical which sterically hinders the OH group, R b  is hydrogen or, if a is 1, can also be a radical of the formula ##STR42## in which K is a direct bond or a divalent group of the formula --S--, --S--S--, --SO--, --SO 2  --, --CH 2  SCH 2  --, --CH 2  OCH 2  --, --CH(R 21 )-- or --N(R 22 )--, in which R 21  is hydrogen, C 1  -C 12  -alkyl, or C 3  -C 15  -alkyl which is interrupted by --S-- or --O-- and R 22  is hydrogen, C 1  -C 18  -alkyl or phenyl, R c  is hydrogen or C 1  -C 8  -alkyl and Z and B are as defined in claim 1. 
     
     
       3. A compound according to claim 1 of the formula ##STR43## in which Z and B are as defined in claim 1, a, b, R a , R b  and R c  are as defined in claim 2 and R d  is C 1  -C 21  -alkyl, C 3  -C 15  -alkoxyalkyl, C 5  -C 12  -cycloalkyl, C 7  -C 13  -aralkyl, phenyl or a radical --C m  H 2m  --CO--V--C n  H 2n  --B, in which m is a number from 1 to 20, n is a number from 1 to 4 and V is --O-- or --N(R 22 )-- wherein R 22  is hydrogen, C 1  -C 18  -alkyl or phenyl, or R d  together with an R c  in the ortho-position and the aromatic ring, is a coumaran or chroman ring, or, if a is 1, R d  can also be a radical of the formula ##STR44## in which s is 1 or 2 and, if s is 1, L is C 2  -C 12  -alkylene, which can be interrupted by one or two O or S atoms, C 4  -C 10  -alkenylene, C 4  -C 6  -alkynylene, C 5  -C 12  -cycloalkylene, xylylene or a radical of the formula ##STR45## --CH 2  CH(OH)CH 2  --, --CH 2  CH(OH)CH 2  --O--R 12  --O--CH 2  CH(OH)CH 2  -- or --CH 2  COO--R 10  --OOCCH 2  -- and R 10  and R 12  are as defined in claim 1 or, if s is 2, L is a trivalent group of the formula ##STR46## 
     
     
       4. A compound according to claim 1 of the formula ##STR47## wherein Z' is an (a+b)-valent organic radical, R e  and R f  are C 1  -C 5  -alkyl, or the two radicals, together with the C atom to which they are bonded, are a cycloalkane or alkylcycloalkane ring, or one of R e  and R f , together with the C atom to which it is bonded and the radical Z' or part of the radical Z' is a cycloalkane or alkylcycloalkane ring,   R d  is C 1  -C 20  -alkyl, C 3  -C 15  -alkoxyalkyl, C 5  -C 12  -cycloalkyl, C 7  -C 13  -aralkyl, phenyl or a radical --C m  H 2m  --CO--V--C n  H 2n  --B, in which m is a number from 1 to 20, n is a number from 1 to 4 and V is --O-- or --N(R 22 ) wherein R 22  is hydrogen, C 1  -C 18  alkyl or phenyl, or R d  together with an R c  in the ortho-position and the aromatic ring, is a coumaran or chroman ring, or, if a is 1, R d  can also be a radical of the formula ##STR48##  in which s is 1 or 2 and, if s is 1, L is C 2  -C 12  -alkylene, which can be interrupted by one or two O or S atoms, C 4  -C 10  -alkenylene, C 4  -C 6  -alkynylene, C 5  -C 12  -cycloalkylene, xylylene or a radical of the formula ##STR49##  --CH 2  CH(OH)CH 2  --, --CH 2  CH(OH)CH 2  --O--R 12  --O--CH 2  CH(OH)CH 2  -- or --CH 2  COO--R 10  --OOCCH 2  -- and R 10  and R 12  are as defined in claim 1 or, if s is 2, L is a trivalent group of the formula ##STR50## R a  is a monovalent hydrocarbon radical which sterically hinders the OH group,   Z is a (1+b)-valent organic linking radical,   B is as defined in claim 1,   R c  is hydrogen or C 1  -C 8  -alkyl,   a and b independently of one another are numbers from 1 to 3 and (a+b) is a number from 2 to 4, and   R b  is hydrogen or, if a is 1, can also be a radical of the formula ##STR51##  in which R c , R a , Z, B and b are as defined above, K is a direct bond or a divalent group of the formula --S--, --S--S--, --SO--, --SO 2  --, --CH 2  SCH 2  --, --CH 2  OCH 2  --, --CH(R 21 )-- or --N(R 22 )--, in which R 21  is hydrogen, C 1  -C 12  -alkyl, or C 3  -C 15  -alkyl which is interrupted by --S-- or --O-- and R 22  is hydrogen, C 1  -C 18  -alkyl or phenyl, or R b  is a radical of the formula ##STR52##  wherein R e , R f  and B are as defined above and Z" is a divalent organic radical.